Having to overcome unexpected problems is a hallmark of entrepreneurship. Almost every business owner, artist, maker, and creative we know has had to deal with countless unexpected problems that arise in the journey and so we asked some brilliant folks from the community to share their stories of the unexpected problems they’ve faced along the way.

Jessica Mason

One of the most unexpected challenges we faced when starting Compass to Paradise was just how much there is to learn when you’re building a brand from scratch. We knew we loved travel, storytelling, and capturing beautiful moments—but we had no idea how many layers existed behind the scenes to actually turn that passion into a business. Read more>>

Wendy Sierra

One of the most unexpected problems I faced in my creative journey was self doubt. I come from humble beginnings and sometimes I felt like my talent did not deserve a space in high-end salons. At times I would abandon projects or not post my work because I feared they weren’t good enough. To resolve this, I had to learn how to separate the creative process from perfectionism. I gave myself permission to create without judgement and from there I became one of the most highly respected color correction stylist in my salon and in all of Long Beach and surrounding areas. I kept furthering my education and surrounded myself with a supportive creative community who I could share my work with and get constructive feedback. I also realized that imperfection is often where originality lives. Read more>>

Shawn Black

Lately, one of the biggest challenges I face is selling my artwork on social media. It’s not only time-consuming but also requires mastering a steep learning curve to effectively position my work on each platform. Beyond creating the artwork itself, I have to take on multiple roles—photographer, photo editor, and social media strategist—understanding how to optimize reels, posts, and stories. Read more>>

Elizabeth Walden

Personalization. When I first started out, the bulk of my work was done in studio with projects such as wedding envelope addressing, place cards, commissioned pieces on paper, etc. While there is still somewhat of a demand for that sort of thing, it has died down quite a bit with the emergence of advanced computerized fonts and printing possibilities. These days, about 95% of my company’s revenue comes from live events. Companies are seeing the benefit of having a live artist on site as an added incentive to their purchases, and the possibilities are endless! I always tell my clients: whatever your product, I will find the right material to personalize it. Read more>>